


Small Gestures

by chilly83



Category: Chicago PD (TV)
Genre: Fluff
Language: English
Status: Completed
Published: 2020-06-18
Updated: 2020-06-18
Packaged: 2021-03-03 22:02:23
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,348
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24792796
Author URL: https://archiveofourown.org/users/chilly83/pseuds/chilly83
Summary: Before he ever even met Detective Upton from Robbery/Homicide, she had already made an impression on Jay.Upstead One-Shot!
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 8
Kudos: 86
Collections: Hailey and Jay One Shots





	Small Gestures

**Author's Note:**

> Hello! Thanks for taking the time to read my fic! I hope you guys like it. I know I should be working on “Hypothetically speaking” but I wanted to do a fluffy one shot! This fic is inspired by a prompt from darkdisrepair on tumblr. If you have never read their work, check them out on tumblr!!! More on the prompt in the end notes.

When Intelligence inherits a case from another unit, they never know what to expect. Usually, the case comes in the form of boxes of files containing reports and field notes from the initial investigators. Usually these notes are detailed enough for them to pick up where the previous investigation stopped. Sometimes, they are not so lucky and they find themselves tracking down the officers to get more information. 

The not so lucky times are the ones Intelligence hates. 

That’s what makes Detective Upton from Robbery/Homicide stand out in Jay’s mind. The ones who make him do extra work always do. Unlike the usual irritation at shotty police work, however, it was her handwriting that made him shake his head.

At first, he was excited to see all the boxes that were sent over. Often, this means a lot of notes and a lot of good police work. Jay knew they had taken over the case because someone they were investigating was linked to it. He felt bad seeing all the work Detective Upton had put in. That quickly went away when he started reading the files.

The first thing he noticed was she was left-handed. He could tell from the way her writing sometimes smeared across the paper. This normally wouldn’t bother him, but the sloppy handwriting had already made it difficult to read. It would have been easier for him to call her and get the information he needed over the phone, but this was always a last resort for Jay. 

Instead, he sat there trying to discern the detectives writing. That’s when he noticed the second thing: Detective Upton’s incredible attention to detail.

Detective Upton would annotate the date, time, location and length of each interaction she had with witnesses or suspects in the margins of her notes. Not only would she take notes on what was said during interviews, she also took notes on what she saw. 

_2/11/17 11 am corner liquor n. hampton_

_Diaz(F) appear 2B nervous. Look shoulder. Averted I’s._

_Child(F)D scared. Look Diaz b4 sp. Posture tense. Long sleeves???_

_13 mins_

She would use shorthand on one side of notes and Jay would find that she wrote out her complete thoughts on the other side. 

_Diaz interviewed at 2197 N. Hampton Rd appeared to be nervous. Looked over shoulder throughout interview. Averted eye contact repeatedly. Child present was Diaz’s daughter. appeared scared. Hid behind Diaz. Would look at mom before answering questions. Wore long sleeves in July. Refer to child services for possible domestic/child abuse._

The third thing Jay noticed was that Detective Upton liked to write out her theories whenever they came to her. He found napkins with thoughts written down and a receipt from Starbucks with some ideas on the back. He couldn’t help but notice the order on the other side: caramel macchiato with extra syrup. He shook his head as he judged her for her life choices.

The last thing he noticed was she seemed to work all day and sometimes into the night on cases. He would notice that her handwriting would progressively get worse as he went through notes. He would then flip a page and see that the writing had become more legible. 

_“Start of a new day”_ he thought to himself. 

_“Losing steam”_ he thought when the notes again became illegible.

After a couple of days of going through her notes, he was able to see what she saw. She knew there was more to the story than just robbing businesses. She had noticed that each store was run by immigrant families. These families had young children with them, all of whom appeared scared and clung to their mothers. She suspected that a local gang was intimidating the families and hurting the kids to get protection money from them.

Jay was able to piece the rest together from there. They had been turned on to the 100 Syndicate gang by a CI. The CI had relayed info that the gang was trying to move in on new territory. When Intelligence began to investigate the tip, they found that over the course of 5 months, multiple family owned businesses had been robbed. 

Jay took the information to his team. 100 Syndicate was trying to take over by getting businesses to pay for protection. Unfortunately, many of these businesses were already under the control of the local gang who ran the territory. These businesses were unfortunately caught in the middle of a gang war. They still didn’t know which side was doing the robbing and killing, but at least they had somewhere to start.

Intelligence was able to close the case a week later and Jay went on with his life. He forgot all about Detective Upton from Robbery/Homicide until 6 months later when another box came across his desk.

He recognized the handwriting on the box immediately and rolled his eyes. It wasn’t because he thought she was a bad cop, he actually thought quite highly of the detective he had never met. Her notes and thoughts on the previous case made solving it a lot easier. It was her handwriting that earned the eye roll.

This time, the first thing he noticed was how small the casefile was. It made sense; the home invasion had just happened 2 days earlier. Intelligence had been assigned the case at the request of the Mayor who wanted it solved ASAP. Still, Jay was surprised at how much work Detective Upton had managed to do in those 2 days.

When he read through her notes this time, he noticed that right from the start the handwriting was almost illegible. He knew the crime scene was discovered in the morning, so he reasoned that it would be easier to read if it followed the previous case’s pattern. He realized then that the notes weren’t written in haste, but rather with a shaky hand. As he read through the details of the case he understood why.

A family of 5, including 3 children, had been murdered. The parents had been tied up and the house ransacked. The children were found in their beds and Detective Upton had theorized they were killed in their sleep. It was one of those cases that every cop hate to get, one with child victims. 

The next thing he noticed on the very last page of notes was the corner of the page. It had a small round area that was slightly wrinkled. He ran his finger over it and then realized what is was. A tear drop. He let out a deep breath and closed the notes. He knew a lot of cops struggled with these cases and the only solace you get from them is putting the culprit in jail. Intelligence had taken that away from Upton.

Thankfully, Intelligence was able to solve the case quickly and get the home invaders off the streets. Jay thought about letting Detective Upton know, but ultimately decided against it. 

As luck would have it, 2 months later his path would once again cross with Detective Upton. This time, it’s Intelligence that responds to the crime scene first. Jay and Erin heard a call come out over the radio while at lunch and were the first officers to respond to the robbery in progress.

They had just begun to brief Hank on the situation when Jay heard an unfamiliar voice giving out orders to the patrol officers.

“I need you outside to set up the tape 50 yards. And roll in the crime lab.” The woman said. 

“All right but-” The officer attempted to speak.

“Now.” She responded with a firm tone.

All 3 stopped and turned towards the ordering detective. Jay first took in her appearance, then instantly noted her firm tone and tense posture. He could tell she was annoyed.

“Detective Upton. Robbery/Homicide.” She said. Jay instantly recognized the name. This is the woman who’s thoughts he had spent hours reading twice this year. Before he gets a chance to say anything, Hank had addressed the detective.

“Hank Voight. Intelligence.”

“Ah.” Hailey responded with slight irritation. She knew the name. “I appreciate the help Sergeant, but as of now this is my scene.”

Erin quirked an eyebrow at the detective’s boldness. Though Hank had not met every officer on the force, she had no doubt everyone knew his name and reputation. She was amused to see the confrontation unfold in front of her.

“My team recovered evidence and saved a woman’s life.” Hank said as he looked Detective Upton in the eyes. “We’re running point.”

Jay watched as Hank turned around and attempted to disengage the detective. His eyes immediately darted to the ground. 

“Make sure those shell casing are photo’d, bagged and tagged.” Upton called out to an officer processing the scene.

The order was enough to make Hank stop in his tracks and turn back to her. Upton could tell the Sergeant was annoyed, but she straightened her stance and continued.

“’Ive been working this crew for the last three weeks.” She stated with a firm tone.

“Huh. Then why did my team respond first?” Hank retorted.

Jay looked from Hank to Upton. He understood her frustration. This would be the third case Intelligence had taken from her this year.

“I’m from Robbery/Homicide. There’s been a robbery and a homicide here. So I’d appreciate it you vacated my crime scene.” Upton said one last time before she walked in between Jay and Hank, effectively ending the conversation. Jay stepped to the side and attempted to hide his smile. It wasn’t often that people stood up to Hank Voight, much less kicked him out of crime scenes. He found himself amused with Detective Upton from Robbery/Homicide.

Unfortunately, the situation would not be resolved as easily as Upton had hoped. Hank made a phone call and got the case moved to Intelligence. Upton had showed up at the district and attempted round 2 with Hank but was immediately shut down by the Chief. She went back to her unit and boxed up her files and notes to send over. 

When the boxes arrived, there were so many that the team had to split them up. Jay already knew what to expect when he started looking through Upton’s notes. The rest of the team, however, had not had to deal with her handwriting yet. Jay chuckled as he watched his team share files and try to decipher her notes. 

It was Al who would ultimately convince Hank to bring Upton on to the case. He made it through 3 pages of notes before he realized that it would be easier to bring Upton on rather than play catch up with all her notes. With one phone call, Jay found himself working side by side with the detective whose handwriting had nearly driven him insane. 

When Hank told Jay that he was going to ask Upton to fill in for Burgess until she got back, he knew he had to do something. He was going to be reading her handwriting for the upcoming weeks. There was nothing he could do about the penmanship, but he could at least do something about the pen. He jumped on Amazon that night and searched for a pen made specially for lefties. With one click, he was able to order it and after a couple of days, he had it in his hands. 

Jay brought it into work the next day and instantly forgot all about it the second they caught a case. It wasn’t until Hailey was packing up to leave for the day that he remembered.

“Hey Upton.” Jay said as she was getting ready to walk down the stairs. He reached into his drawer and pulled the pen out. “I got you something.” He said as he walked to her.

The pen was still in its original packaging. Hailey watched him with confusion as he approached her holding out something that appeared to be office supplies. 

She reached out to take it from him and read the label. 

_Sarasa Series Pen. Rapid Dry Technology_

Jay watched her eyes read over the label with confusion.

“I noticed you were a lefty.” He said. He didn’t think it would be a big deal, but her reaction made him worry he had done something wrong.

He watched her eyes widen as she stared at the pen. He thought he saw them start to shine, as if they were tearing up.

“I thought- I know lefties have a hard time with pens.” He said, trying to explain the pen. “I thought it could help with smears.” He was starting to worry he had inadvertently offended her. 

Before he could worry too much, he saw a smile creep across Hailey’s face. He watched her eyebrows quirk as she nodded her head.

“Ya.” Hailey finally said. She took a deep breath and tried to release it slowly. She couldn’t remember the last time she received a gift for no reason. The small gesture had momentarily left her speechless. “I do have a hard time with smears.” She said with a chuckle as she held up her left hand. Jay could see the ink smears on the side of her pinky and fist. 

It wouldn’t be the only pen he would buy her. In fact, over the course of their lives together, he would buy many more. When he noticed the smears on her hands come back, he started keeping spares in his desk. He would buy them when she would lose it, or the pen ran out of ink. When they moved in together, he made sure to keep some on hand in their kitchen junk drawer. He bought them years later as stocking stuffers for her and later for their son, who also turned out to be a lefty.

Each time she got a new one, Hailey would have to same reaction she had when she was given the first one. It was all the motivation Jay needed to keep buying them. 

**Author's Note:**

> Darkdisrepair had the fun idea that Jay knew who Hailey was before they worked on the Spann case together because of her bad handwriting. Since Intelligence often takes cases from other units, this is how Jay would’ve come across her files. Darkdisrepair gave me permission to take their prompt and turn it into a one shot! I had a lot of fun writing it and I hope you enjoyed reading it! I hope to update my other fic this weekend (just in case that’s something you’ve been following). As always, thanks for reading and thanks to the Let’s Talk Upstead group chat on tumblr for the ideas and support!


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